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Family-Friendly Chicago Itinerary Featuring Deep-Dish Pizza & Iconic Attractions: May 9-12, 2025

Viewed by 88 travelers

Day 1: Lunch & Navy Pier

Chicago, USA on May 9, 2025

1:00pm

Check-in & Settle at Hyatt Regency O'Hare

Unpack and get ready for your afternoon excursion in Chicago.
Included, 30m

1:30pm

Transit from Hyatt Regency O’Hare to Navy Pier via Blue and Red Lines

Walk to O'Hare Blue Line station and take the train toward downtown to Clark/Lake station (~45 mins), then transfer to Red Line to Grand station (~5 mins), followed by a 12-minute walk east to Navy Pier.
USD5 per person for unlimited day pass, 1h

2:30pm

Lunch at Riva Crabhouse on Navy Pier

Family-friendly restaurant at Navy Pier offering seafood and kid-approved options with scenic lakefront views.
USD25 per person, 1h

3:30pm

Explore Navy Pier

Enjoy the Centennial Wheel, Chicago Shakespeare Theater, and stroll along the waterfront area.
Centennial Wheel USD18 per person, 1h

4:30pm

Return to Hyatt Regency O’Hare

Take Red Line from Grand to Clark/Lake and transfer to Blue Line toward O’Hare (~1h).
Included in day pass, 1h
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Day 2: Grant Park & Deep-Dish Pizza Dinner

Chicago, USA on May 10, 2025

8:00am

Breakfast at Yolk near Hyatt Regency O’Hare

Enjoy a hearty breakfast with diverse options to prepare for the day.
USD15 per person, 1h

9:00am

Relax at the Hotel

Enjoy hotel amenities and rest until afternoon.
Free, 7h30m

4:30pm

Blue Line L Train from O’Hare to Jackson Station

Travel about 45 minutes to downtown Chicago.
USD3 per person, 45m

5:15pm

Walk 10 minutes to Grant Park

Explore Chicago’s iconic park and beautiful Buckingham Fountain at dusk.
Free, 15m

5:30pm

Stroll Grant Park & See Buckingham Fountain

Enjoy gardens, walking paths, and the famous fountain’s illuminated evening display.
Free, 1h

6:30pm

Dinner at Giordano's Deep-Dish Pizza near Grant Park

Taste Chicago’s renowned deep-dish pizza in a family-friendly setting, perfect for a filling and iconic meal.
USD25 per person, 1h15m

7:45pm

Return Blue Line from Jackson to O’Hare

Take the train back to your hotel for a restful night.
USD3 per person, 45m
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Day 3: Lincoln Park Zoo & Tapas

Chicago, USA on May 11, 2025

2:00pm

Transit from Hyatt Regency O’Hare to Lincoln Park Zoo

Take Blue Line to Clark/Lake, transfer to Red Line northbound to Fullerton station (~1h), then a 10-minute walk to the zoo.
USD3 per person, 1h

3:10pm

Visit Lincoln Park Zoo & Conservatory

Explore the free zoo and beautiful conservatory, great for children and adults alike.
Free, 1h30m

4:40pm

Dinner at Café Ba-Ba-Reeba!

Enjoy a family-friendly Spanish tapas restaurant near Lincoln Park with flavorful and diverse dishes.
USD25 per person, 1h

6:00pm

Return to Hyatt Regency O’Hare

Take Red Line back to Clark/Lake, then Blue Line to O’Hare, about 1 hour total transit time.
USD3 per person, 1h
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Day 4: Riverwalk, Skydeck & Deep-Dish Finale

Chicago, USA on May 12, 2025

9:00am

Pack and Check-out

Prepare for your last day of sightseeing; leave luggage at the hotel for collection after tours.
Free, 1h

10:00am

Blue Line L Train to Washington Station

Take approximately 45 minutes downtown.
USD3 per person, 45m

10:45am

Walk to Starbucks Reserve Roastery

Enjoy a 15-minute walk to this unique coffee experience with delicious treats for the family.
Free, 15m

11:00am

Visit Starbucks Reserve Roastery

Watch coffee roasting in action and enjoy specialty drinks while kids savor snacks.
Free, 1h

12:00pm

Lunch at Beatrix on Chicago Riverwalk

Family-friendly restaurant with fresh ingredients and options for kids, set along the scenic riverwalk.
USD20 per person, 1h

1:00pm

Chicago Architecture River Cruise

90-minute architectural boat tour departing from Michigan Ave and Wacker Drive dock, showcasing Chicago’s famous buildings from the river.
USD53 adult, USD41 child, 1h30m

2:30pm

Walk to Willis Tower Skydeck

A 15-minute walk to Willis Tower for panoramic city views and the thrilling Skydeck glass ledge experience.
USD35 adult, USD28 child, 1h

3:45pm

Dinner at Lou Malnati's Deep-Dish Pizza

Enjoy a final iconic Chicago deep-dish pizza meal in a warm, family-friendly atmosphere before heading back to the hotel.
USD25 per person, 1h

4:45pm

Return to Hyatt Regency O’Hare

Walk back to Washington station and take Blue Line train to O’Hare (approx. 45 minutes).
USD3 per person, 45m
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